Reactions of α-carbanions of lithium acylates with N,N-diethyl-N-chloro- and N,N-diethyl-N-bromoamines

被引:3
|
作者
Zorin, A. V. [1 ]
Zainashev, A. T. [1 ]
Zorin, V. V. [1 ]
机构
[1] Ufa State Petr Technol Univ, Ul Kosmonavtov 1, Ufa 450062, Russia
关键词
alpha-halocarboxylic acid; dicarboxylic acid; N; N-diethyl-alpha-haloamine; alpha-carbanions of lithium acylates; nucleophilic substitution; oxidative coupling;
D O I
10.1134/S1070363216110116
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The interaction of alpha-carbanions of lithium acylates (prepared via metalation of acetic, butyric, or isobutyric acid with lithium diisopropylamide in tetrahydrofuran under argon atmosphere) with N,N-diethyl-N-chloro- or N,N-diethyl-N-bromoamine has resulted in the formation of succinic acid or its 2,3-diethyl- and 2,2,3,3-tetramethyl-substituted derivatives in yields of 47-66% and the corresponding alpha-halocarboxylic acids (12-34%). Anion-radical scheme of the reaction products formation has been suggested.
引用
收藏
页码:2469 / 2472
页数:4
相关论文
共 50 条
  • [31] Interactions of bovine brain tubulin with pyridostigmine bromide and N,N′-diethyl-m-toluamide
    Prasad, V
    Scotch, R
    Chaudhuri, AR
    Walss, C
    Fathy, DB
    Miller, C
    Ludueña, RF
    NEUROCHEMICAL RESEARCH, 2000, 25 (01) : 19 - 25
  • [32] Orthoamides and Iminium Salts, IC. Synthesis and Reactions of N,N, N′, N′,N"-Pentaalkyl-N"-[2-(N,N, N′, N′,N"-pentaalkylguanidinio)ethyl]-guanidinium salts
    Kantlehner, Willi
    Tiritiris, Ioannis
    Frey, Wolfgang
    Kress, Ralf
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2020, 75 (6-7): : 685 - 695
  • [33] Crystal structure of bis(μ-chloro)-bis[chloro(N,N,N′-trisbenzylethylenediamine)copper(II)]
    Ma, PG
    Zhang, MJ
    Yang, QC
    Yuan, DY
    Yu, JG
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2005, 21 (05) : 744 - 748
  • [34] Electrochemical degradation of N,N-diethyl-m-toluamide on a boron-doped diamond electrode
    Chen, Te-San
    Chen, Pi-Hui
    Huang, Kuo-Lin
    JOURNAL OF THE TAIWAN INSTITUTE OF CHEMICAL ENGINEERS, 2014, 45 (05) : 2615 - 2621
  • [35] Spectroscopic and theoretical studies of some N,N-diethyl-2-[(4′-substituted)phenylsulfonyl]acetamides
    Vinhato, Elisangela
    Olivato, Paulo R.
    Rodrigues, Alessandro
    Zukerman-Schpector, Julio
    Dal Colle, Maurizio
    JOURNAL OF MOLECULAR STRUCTURE, 2011, 1002 (1-3) : 97 - 106
  • [36] γ-ray damage of N,N-diethyl-hydroxylamine in water and its radiolytic products at lower dose
    Wang, J. H.
    Wang, C. C.
    Wang, Sh. X.
    Wu, M. H.
    Xu, G.
    Zheng, W. F.
    He, H.
    Zhang, Sh. D.
    JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY, 2016, 309 (02) : 503 - 510
  • [37] A spectrophotometric method for measuring permanganate index (CODMn) by N,N-diethyl-p-phenylenediamine (DPD)
    Pang, Zijun
    Cai, Yajuan
    Xiong, Weihao
    Xiao, Junyang
    Zou, Jing
    CHEMOSPHERE, 2021, 266
  • [38] SYNTHESIS, STRUCTURE AND REACTIONS OF SOME ORGANYL-BIS[N-(N',N',N'', N''-TETRAMETHYL)GUANIDINYL]PHOSPHINES AND DIORGANO-[N-(N',N',N'',N''-TETRAMETHYL)GUANIDINYL]PHOSPHINES
    MUNCHENBERG, J
    BOGE, O
    FISCHER, AK
    JONES, PG
    SCHMUTZLER, R
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 86 (1-4): : 103 - 121
  • [39] PREPARATION AND REACTIONS OF N-PHENACYL-N-TOSYLHYDROXYLAMINES AND N-PHENACYL-N-TOSYLHYDRAZINES
    WESSIG, P
    HENNING, HG
    LIEBIGS ANNALEN DER CHEMIE, 1991, (10): : 983 - 986
  • [40] Orthoamides, LXIX. Contributions to the Synthesis of N,N,N′,N′,N"-peralkylated Guanidines and N,N,N′,N′,N",N"-persubstituted Guanidinium Salts
    Kantlehner, Willi
    Mezger, Jochen
    Kress, Ralf
    Hartmann, Horst
    Moschny, Thorsten
    Tiritiris, Ioannis
    Iliev, Boyan
    Scherr, Oliver
    Ziegler, Georg
    Souley, Bahari
    Frey, Wolfgang
    Ivanov, Ivo C.
    Bogdanov, Milen G.
    Jaeger, Ulrich
    Dospil, Guenther
    Viefhaus, Tillmann
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2010, 65 (07): : 873 - 906